O[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[OH-:10].[Na+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]>C(O)C>[CH2:13]([O:7][CH:6]([OH:10])[C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]First, 12.80 g (0.10 M) of 4-hydroxybenzyl alcohol (compound (8)) was dissolved in ethanol 190 mL, and 4.0 g (0.10 M) of sodium hydroxide was added thereto. The resulting mixture was heated to 65° C. After heating, 24.14 g (0.11 M) of 10-bromo-1-decene (compound (22)) prepared in Synthetic example 1-1 was added dropwise, and the resulting mixture was aged at a mixture temperature of 76° C. for 6 hours. Next, the generated salt was removed by decantation, and the reaction solution was concentrated. After concentration, the resulting solution was diluted with 350 mL of diethyl ether and washed twice with 100 mL of deionized water. After washing, the organic layer was concentrated to produce crude crystals. The crude crystals were recrystallized twice from 25 mL of hexane. The recrystallized crystals were washed with hexane and dried. Thereby, 16.88 g of 9-decenoxybenzyl alcohol (compound (23)) was produced (yield: 64.3%).
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